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12.3.1.4.3.5 Method 5: Reactions of α-Aminonitriles with Aldehydes or Ortho Esters

DOI: 10.1055/sos-SD-012-00398

Grimmett, M. R.Science of Synthesis, (200212380.

When 2,4(5)-disubstituted imidazoles are formed by reaction of 2-aminonitriles with aldehydes, the aldehyde provides the C2 substituent.[‌235‌,‌236‌] With benzaldehyde, (methylamino)phenylacetonitrile gives 1-methyl-2,5-diphenyl-1H-imidazole in 76% yield.[‌236‌] If an orthoformate is used in place of the aldehyde, the products are 1H-imidazol-4(5H)-ones. Thus, refluxing aminoacetonitrile hydrochloride for about 30 minutes with trimethyl orthoformate produces a small amount of 1H-imidazol-4(5H)-one along with (formamido)acetonitrile as the major product.[‌237‌,‌238‌] As the N-substituted α-aminonitriles can be made rapidly by a mild, one-pot combination of aldehyde, primary or secondary amine, and chlorotrimethylsilane in methanol,[‌239‌] this general approach may have further applications.

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